N,N-Dimethylmethyleneiminium chloride
| Empirical Formula (Hill Notation): | C3H8ClN |
| Linear Formula: | CH2=N+(CH3)2Cl- |
| CAS Number: | 30354-18-8 |
| Molecular Weight: | 93.56 |
| Beilstein/REAXYS Number: | 505955 |
| EC Number: | 250-142-4 |
| MDL number: | MFCD00011809 |
| PubChem Substance ID: | 57650016 |
| NACRES: | NA.22 |
| Кат. номер |
| 40766-INTR |
| 40766-5G |
| 40766-25G |
N,
N-Dimethylmethyleneiminium chloride (Bohmes salt) is a dimethylaminomethylating agent that can be used as one of the key reagents in the following applications:
- Electrophilic aminomethylation of aldehydes and ketones to synthesize corresponding Mannich products, also known as Mannich reaction.
- Preparation of dihydronaphthyridinones as HIV-1 integrase inhibitors.
- Preparation of cyanotetrahydrooxo--carbolines via cyclocondensation of cyanomethyl indole-2-carboxylate with ammonia.
- Asymmetric synthesis of phalarine via stereospecific Pictet-Spengler cyclocondensation and traceless chirality transfer from L-tryptophan.
- Synthesis of functionalized diarylpyrrolizines as inhibitors of microsomal prostaglandin E2 synthase-1 (mPGES-1) and 5-lipoxygenase (5-LOX).
- Synthesis of (±)-phalarine with the rearrangement of an azaspiroindolenine and Gassman oxindole preparation as key steps.
Reacant for:
Preparation of dihydronaphthyridinones as HIV-1 integrase inhibitors
Mannich reactions
Preparation of cyanotetrahydrooxo--carbolines via cyclocondensation reactions
Asymmetric synthesis of phalarine via stereospecific Pictet-Spengler cyclocondensation and traceless chirality transfer from L-tryptophan
Synthesis of functionalized diarylpyrrolizines as inhibitors of microsomal prostaglandin E2 synthase-1 (mPGES-1) and 5-lipoxygenase (5-LOX)
Synthesis of (±)-phalarine with the rearrangement of an azaspiroindolenine and Gassman oxindole preparation as key steps
5, 25 g in glass bottle
"Mannich-reagent" for direct use; higher yields of purer products were achieved in shorter times compared with the classical "Mannich reaction"; in-situ preparation of the reactive triflate with TMS-triflate
| Quality Level | 100, |
| assay | 95.0% (AT) |
| reaction suitability | reaction type: C-C Bond Formation |
| mp | 146-148 °C (lit.) |
| SMILES string | [Cl-].C[N+](C)=C |
| InChI | 1S/C3H8N.ClH/c1-4(2)3;/h1H2,2-3H3;1H/q+1;/p-1 |
| InChI key | ZJTROANVDZIEGB-UHFFFAOYSA-M |
| pictograms | GHS02,GHS07 |
| signalword | Warning |
| hcodes | H228 - H315 - H319 - H335 |
| pcodes | P210 - P302 + P352 - P305 + P351 + P338 |
| Target Organs | Respiratory system |
| Personal Protective Equipment | dust mask type N95 (US),, Eyeshields,, Gloves, |
| RIDADR | UN1325 - class 4.1 - PG 3 - Flammable solids, organic, n.o.s., HI: all |
| WGK Germany | WGK 3 |
| Flash Point F | 179.6 °F - closed cup |
| Flash Point C | 82 °C - closed cup |